【结 构 式】 |
【分子编号】51403 【品名】1-[benzyl[2-(2-methoxyphenoxy)ethyl]amino]-3-chloro-2-propanol 【CA登记号】 |
【 分 子 式 】C19H24ClNO3 【 分 子 量 】349.8572 【元素组成】C 65.23% H 6.91% Cl 10.13% N 4% O 13.72% |
合成路线1
该中间体在本合成路线中的序号:(V)This compound has been obtained in two related ways: 1. The reaction of 2-(2-bromoethoxy)anisole (I) with benzylamine (II) by heating at 80 C gives the secondary amine (III), which is condensed with epichlorohydrin (IV) by heating at 60 C to yield the isopropanol derivative (V). The condensation of (V) with 4-hydroxycarbazole (VI) by means of K2CO3 in refluxing dioxane affords the adduct (VII), which is finally debenzylated by hydrogenolysis with H2 over Pd/C in ethanol/water. 2. The condensation of the secondary amine (III) with 4-(2,3-epoxypropoxy)carbazole (VIII) in refluxing ethanol gives the already reported adduct (VII), which is debenzylated as indicated.
【1】 Seres, P.; Cselenyak, J.; Nagy, K.; Simig, G.; Gregor, T.; Nagy, P.K.; Greff, Z.; Balazs, L.; Barkoczy, J.; Vereczkey, G.D.; Nemeth, N.; Szabo, T.; Ratkai, Z.; Doman, I. (Egis Pharmaceuticals Ltd.); Process and intermediates for preparing 1-[9'H-carbazol-4'-yloxy]-3-[2''-(2'''-methoxy-phenoxy)ethyl]amino]-propan-2-ol (carvedilol). EP 0918055 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 51402 | 2-(2-Bromoethoxy)methoxybenzene; 1-Bromo-2-(2-methoxyphenoxy)ethane | 4463-59-6 | C9H11BrO2 | 详情 | 详情 |
(II) | 15147 | Benzylamine; Phenylmethanamine | 100-46-9 | C7H9N | 详情 | 详情 |
(III) | 30528 | N-benzyl-2-(2-methoxyphenoxy)-1-ethanamine; N-benzyl-N-[2-(2-methoxyphenoxy)ethyl]amine | C16H19NO2 | 详情 | 详情 | |
(IV) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
(V) | 51403 | 1-[benzyl[2-(2-methoxyphenoxy)ethyl]amino]-3-chloro-2-propanol | C19H24ClNO3 | 详情 | 详情 | |
(VI) | 29480 | 4-Hydroxycarbazole; 9H-carbazol-4-ol | 52602-39-8 | C12H9NO | 详情 | 详情 |
(VII) | 51404 | 1-[benzyl[2-(2-methoxyphenoxy)ethyl]amino]-3-(9H-carbazol-4-yloxy)-2-propanol | C31H32N2O4 | 详情 | 详情 | |
(VIII) | 40171 | 9H-carbazol-4-yl 2-oxiranylmethyl ether; 4-(2-oxiranylmethoxy)-9H-carbazole | 51997-51-4 | C15H13NO2 | 详情 | 详情 |